Fast like Twista but hilarious like the Lonely Island crew, actor and writer David Burd became rapper Lil Dicky in 2013 when he dropped the megahit "Ex-Boyfriend." Busting out of the Philadelphia suburbs, Burd graduated from the Richmond Robins School of Business in 2010 at the top of his class. A move to San Francisco came next, then he began working on Lil Dicky, writing rhymes, cutting demos, and storyboarding videos for two years before he showed them to the public. He first saw rapping as a way to transfer musical success into television and film writing success, but when he posted "Ex-Boyfriend" and reached a million views within the week, hip-hop lover Burd realized his hip-hop dream was already a reality. The 2013 hit landed on the So Hard mixtape that same year, while "White Crime" ("Walk into the movie with my pants full/Twix, bag of chips, plus a Snapple") dropped in 2014. "Classic Male Pregame" landed a year later, along with Dicky's debut album, Professional Rapper, which featured guest appearances from Snoop Dogg, Fetty Wap, Hannibal Buress, and more, as well as the single "$ave Dat Money" with Fetty Wap and Rich Homie Quan. The effort debuted at number seven on the Billboard 200 and topped the Top Rap, Comedy, and Independent Albums charts, becoming one of the biggest indie releases of the year. Following a 2017 EP from his side project Brain, Lil Dicky returned with 2018's "Freaky Friday," a collaboration with Chris Brown. ~ David Jeffries